Process for preparing urethanes



preparation of tanning agents, insecticides; and

. In preparing the raw materials for the practice reaction period the temperature is raised to 120 ing hexyl alcohol, dodecyl alcohol, hexadecyl alcohol, octadecyl alcohol, octadecenyl alcohol, hy-

I may be used in connection with the reaction, one pletion,

Patented Sept. 2, 1941 I I v p UNITED QTATES: PATENT OFFICE v I rnocass non gig;

misstatement-est Patent Corporation, New York, N. Y, a com J ration oi New York No Drawing. Application February 27, 1939, Se-

rial No. 258,731- In Germany April 8, 1938 7Claims. (o1. 260-452) v This invention relates to a process for producthanes in accordance with the preferred embodiing urethanes', particularly higher molecular urement of the invention, a higher molecular alkyl thanes. More specifically the invention relates ester of chlorcarbonic acid is heated to a high to the production of urethanes by reacting cyclic temperature, a powdered'ammonium salt of the or acyclic organic esters of chlorcarbonic acid 5 nature hereinbeiore described is gradually added, with ammonia-generating ammonium salts. I the heat ng prefe ably Continued t0 3 higher The urethanes obtained in accordance with this perature until the reaction is complete. The process are valuable intermediate products in the temperatures u ed a y somewhat with the spepreparation of a variety of commercially valuable clfic raw materials employe I chemical compounds. The higher molecular 10 The invention will be clearly understood from, urethanes are especially suitable for the preparabut 18 11013 restricted t following example tion of textile assistants, for example, in renderwher e Parts are exp e d in parts by 4 ing textiles as well as other materials water-rea pellent. They are also suitable for use in the Example numerous other chemicals I One hundred parts of chlorcarbonic acid octa- As raw materials'in the process of the instant decyl ester are f f in a Vessel invention chlorcarbonic acid esters 01' all types Provided with a Then While Stirring 40 can be used. These esters can be obtained acparts of finely ground ammonium carbonate are cording to known procedures s phosgene 20 slowly added in portions. Near the end of the C. The reaction goes to completion. The reaction material'is then dissolved in a suitable sol vent for the octadecyl urethane, whereby the inorganic salt'precipitates after which it is filtered f out and the solution evaporated to recover the urethane. If it is desired to-obtain the octadecyl urethane in a purer state, the reaction product is dissolved in 300 parts of alcohol, filtered and crystallized after filtration. The octadecyl ure-, thane can be also freed'from the inorganic materials simply by washing with water.

of the preferred embodiment of the invention, phosgene is reacted with higher molecular alcohols to give esters. As examples of raw materials one can use chlorcarb'onic acid esters of aliphatic alcohols, such as, propyl alcohol, and especially the higher molecular compounds includdroxyoctadecenyl alcohol; cyclic alcohols such as cyclohexanol, methylcyclohexanol, higher molecular alkyl substituted cyclohexanols, naphthenyl It Should be underst ood thatthe present inalcohols, abletyl alcohol, and other resin alcohols, vention is not limited to thevspecmc materials v benzyl alcohol, phenols and naphthols, higher a I compounds, and their uses as herein disclosed, but molecular alkyl phenols and naphthols, and like that it extends to all equivalents which one,

alcohols. The hydrocarbon radicals of these skilled in the art would consider within the pub chlorcarbonic acid esters may be interrupted by port of the instant discl'osure a Within the or contain heteroatoms or heteroatomic groups, scope of theclalms' such valid the like. atomic 40 Instead of the chlorcarbonic acid esters in gengroups containing these atoms, as, for examp eral thehalogen carbonic acid esters are appliesy y radicals and ester ble as bromoand iodocarboni'c acid esters.

In accordance with the process of the invention I claim; these chlorcarbonic acid esters are reacted with 1. Process for preparinghigher molecular reammonlum salts which 'give ofl ammon a 9 thanes which comprises heatinga higher molecuc al y t o e d ri d fr m w ak acids. such s lar chlorcarbonic acid ester and adding thereto monium carbonateammonium acetate, and the a finely divided ammonium ,11; of weak acid lik In this reaction the chlorine atom of the which liberates ammonia under the conditions of various esters is substituted by a NH: radical and the reaction and continuing. the reaction under the urethanes are formed. Although a solvent heat until the reaction goes substantially to comof the advantages of the process is that it does 2. Process for preparing octadecyl urethanes not require its use. Similarly the use of a gaswhich comprises heating a chlorcarbonic acid forming reaction component is not essential. ester of octadecyl alcohol with an ammonium salt In the production of higher molecular ureof a weal; acid which liberates ammonia at the which comprises heating said ester with ammo- 'nium acetate in the absence of a solvent at a temperature which liberates ammonia and continuing the heating until the reaction goes to substantial completion.

6. The process of producing urethanes unsubstituted on the nitrogen atom which comprises reacting an ester of chlorcarbonic acid with an ammonium salt of a weak acid which liberates ammonia under the reaction conditions, said reaction taking place in the absence of solvents.

7. The process for preparing urethanes which comprises reacting a haiocarbonic acid ester with an ammonium salt of a weak acid, which delivers ammonia under the conditions of the reaction.

WOLFGANG G'U'NDEL. 

